Hydrochloric Acid → N-Allyl,N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

HRID 1010783Notes

Reaction equation

HRID 1010783 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:15])=[O:4].C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[CH2:26](Br)[CH:27]=[CH2:28].Cl>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH2:28]([N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[I:15])[C:3](=[O:4])[C:2]([F:16])([F:1])[F:17])[CH:27]=[CH2:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 22292821N-trifluoroacetyl-2-iodo-4-chlorophenethylamine

Product 1

HCID 24773729N-Allyl,N-trifluoroacetyl-2-iodo-4-chlorophenethylamineYield 75.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A solution of N-trifluoroacetyl-2-iodo-4-chlorophenethylamine (0.94 g, 2.4 mmol) in toluene (25 mL) was treated with K2CO3 (0.43 g, 3.12 mmol), KOH (0.40 g, 7.2 mmol), n-Bu4NBr (0.077 g, 0.24 mmol) and allyl bromide (0.43 g, 3.6 mmol) sequentially. The mixture was stirred at 80 C for 3.5 hours, cooled to 20 C and acidified with 10% aqueous HCl. The phases were separated, the aqueous phase extracted with ether (100 mL), the combined organic phases were washed with brine (50 mL), dried with Na2SO4 and concentrated to give 0.76 g of a clear oil. MS calculated for C13H12ClF3INO+H: 418, observed: 418.

Workup

  1. temperaturecooled to 20 C
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with ether (100 mL)
  4. washthe combined organic phases were washed with brine (50 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9c572701d6264b7b9822bbf6ae66a1e7
Source dataset
uspto-grants-2011_07
Patent number
US07977329B2

Reaction notes

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